Used to be, people maintained literal personal phonebooks. Books into which they scrawled the names, numbers, and addresses of their friends and family members. Those were dark times.

In 2014, there’s no need for such old-fashioned foofaraw. Your Mac and iOS devices can sync all your contacts for you, and store more data than those books of yore could have handled even if you wrote with the sharpest of number two pencils. There are plenty of ways to deal with your contacts’ information, so which method do you choose?

There are plenty of ways to deal with your contacts’ information, so which method do you choose?

I spoke with Apple experts Glenn Fleishman, John Moltz, Jaimee Newberry, David Sparks, and Marco Tabini about how they organize their contacts. The upshot: No one’s thrilled with how they organize that Rolodexical data, but there are numerous approaches that work “well enough.”

How they sync contacts

Making sure that you can access every address in your address book on all your devices is a top priority for contact management. Syncing contacts is a big deal.

You have options: For example, you can use iCloud to sync contacts between Apple devices (iPhones, Macs, iPads) or you can use services like Google or Microsoft Exchange to sync instead—particularly if you need to sync your contacts with non-Apple devices, or if you just question iCloud’s reliability.

Each of the five experts I spoke to uses iCloud for contact syncing; I’m the lone outlier who relies on Google’s syncing instead. But the reliance on iCloud, at least on occasion, seems at best unenthusiastic:

Each of the five experts I spoke to uses iCloud for contact syncing; I’m the lone outlier who relies on Google.

Macworld senior contributor Glenn Fleishman said his dependence on iCloud “is stupid of me, as I shouldn’t trust it.” But another contributor, Marco Tabini, said that “so far, iCloud does an admirable job of keeping everything in sync and safe from loss.”

Macworld contributor and cohost of the Mac Power Users podcast David Sparks sticks with iCloud because “Microsoft Exchange has been a little more spotty. I think part of my hang-up is I remember how terrible contact syncing was back in the Palm Pilot days. That platform used to randomly make multiple copies of contacts with no rhyme or reason.” When Sparks runs into trouble now, he uses the $5 app Contacts Cleaner to eliminate duplicates and fix other issues.

How they organize their contacts

For organizing their contacts, every Mac expert I spoke to relies on Apple’s own Contacts apps on the Mac and iOS. Again, I’m the lone outlier, clinging to Google’s (horrendous) contact-management tools on the Web—mostly due to inertia: I started using Google’s contact management before iCloud existed, and I just haven’t taken the time to switch.

Jaimee Newberry—a speaker, writer, and podcast host—doesn’t only use Contacts; she also uses the Web service and app Sincerely to manage mailing addresses. She likes the service in part because it makes quick work of sending actual postal mail from a computer or iOS device, so she relies on it for managing those addresses.

For organizing their contacts, every Mac expert I spoke to relies on Apple’s own Contacts apps on the Mac and iOS.

Sparks, who is also a lawyer, occasionally considers a move beyond Contacts: “Part of me really wants to geek out with one of those online customer relationship managers to handle all my calls to clients, lawyers, and everyone else I deal with in my day job…. Instead I keep it simple and use the Apple Contacts application to sync my personal iCloud contacts and my office’s Exchange-based contact list.”

How they add contacts

Still, Sparks doesn’t love adding or editing his contacts with Apple’s Contacts. “It takes far too many mouse clicks to get things rolling.” Although he stores his contacts in Apple’s app, he also uses the free (with in-app purchases) Cobook app, “which is much faster and always rests in my menu bar.”

Sparks stores his contacts in Apple’s app, but also uses Cobook, ‘which is much faster and always rests in my menu bar.’

Cobook, which I only looked at on Sparks’s recommendation, can merge contact data from various places, including—for free—Facebook, Google, and Twitter. It can work either from the addresses stored in the Contacts app (which, in general, live in your iCloud account) or from your Google contacts. Updating contact data in Cobook definitely takes fewer steps than using the Contacts app, and the changes you make sync quickly via whichever service you rely on.

Cobook can help organize and update your address book from your Mac’s menu bar—regardless of which service you use to sync your contacts.

Tabini uses the Contacts app on his iPhone to add contacts, but when he’s adding new entries into the database on his Mac, he actually relies on Apple’s Mail app: “I’ve found Mail’s data detectors to work well most of the time—they make adding new contacts fairly convenient, at least compared to doing so by hand.”

How they share contacts (when they share at all)

You’ll see three options for sharing a contact—via email, Message, and AirDrop—when you click the ‘Share the current card’ arrow on the Mac.

Both OS X and iOS aim to make it easy to share contact information through email, Messages, Mail, or AirDrop, which is especially useful when you need to give your information to someone in lieu of a traditional business card.

Tabini offered up a tip: “Make sure you keep a contact for yourself, with all your current email, address, and phone coordinates handy, so that you can quickly share it with others…. It’s such a simple way to be ready whenever you need to hand off your information to someone without having to fumble through your contacts—or, worse, having to tell someone your phone number.”

Says Tabini: ‘Make sure you keep a contact for yourself, with all your current email, address, and phone coordinates handy, so that you can quickly share it with others.’

Most of the experts didn’t care much about sharing features, though. Fleishman and Newberry both said that they don’t share contact information with others. Said Moltz: “Occasionally I will share a contact with my wife. I usually do that via emailing the contact card to her.”

How they manage contacts

Managing your contacts—keeping them up-to-date and error-free—takes work. And keeping them truly organized takes even more work.

“I’m terrible at it,” Fleishman said, regarding his own contact management. Newberry shared a similar sentiment with slightly more colorful language.

Sparks, however, offered up some tips on his approach for keeping contacts organized. Chief among them is to make good use of the Notes field (which you can access in both Cobook and Contacts).

Sparks’s chief recommendation for keeping contacts organized is to make good use of the Notes field.

“I add lots of data there that doesn’t fit anywhere else,” he says. “I may keep Lex’s favorite Starbucks drink or a list of important conversations we’ve had if we are working on a project together.”

For quick searching, Sparks also employs what he calls “rudimentary tags” in the Notes field, like #referral or #holidaycard. That makes it easy for him to quickly search for all contacts with that tag, on demand. “I understand I could do the same thing with additional Contacts groups, but I try to keep the number of groups down to a dull roar—and searching contacts for a few tags works just fine.”

David Sparks makes extensive use of the Notes field in his Contact records. That way, he can easily remember—or search for—notes about the folks he's connecting with.

Complaints department

A couple of the experts I spoke to aired a few grievances about contact management within Apple’s ecosystem. “The biggest problem for me is the OS X Contacts interface,” Sparks said. “Things got better with 10.9 Mavericks, but it still involves way too many mouse clicks to change someone’s phone number.”

Sparks also runs into issues where Contacts tries too hard to combine multiple contacts into a single person—in those rare instances where he knows multiple people with the same name: “That never works out well.”

Fleishman said, “I wish that I could have something today that seemed as good at contact/calendar/to-do integration as the old Now Up-To-Date/Now Calendar. For all its horribleness, [that system] actually all flowed together.” He longs for “a BusyCal-style approach that could suck in Google, iCloud, and so on, and sync, automatically, while also giving him control over how he shares events and contact information with other people.”

So what have we learned?

None of the five experts have encountered syncing catastrophes with iCloud, which is a good sign. Interestingly, Apple’s own apps—like many others—are pretty good at handling contact data from multiple sources; so even as a Google-based contact-syncer, I’m able to use Apple’s apps (and now Cobook!) to manage my address book.

The best advice I gleaned from the folks I spoke to is that you need to find some consistent approach to handling contacts.

The best advice I gleaned from the folks I spoke to is that you need to find some consistent approach to handling contacts. I occasionally hear from friends with contact-syncing issues—only some contacts from their iPhones appear on their Mac, for instance. Invariably, they’re unknowingly syncing their contacts in multiple, simultaneous ways. They’ve stored some contacts in Google, others in iCloud, and a few only on the device itself.

To make your contacts appear predictably, you need to know where you’re storing them. Explore alternative apps that don’t create their own databases, but that—like Cobook—make working with your existing address book more efficient. Also, avoid adding contacts via the Mac’s Contacts app when possible; it just takes too many clicks.

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Lex uses a MacBook Pro, an iPhone 5, an iPad mini, a Kindle 3, a TiVo HD, and a treadmill desk, and loves them all. His latest book, a children's book parody for adults, is called "The Kid in the Crib." Lex lives in New Jersey with his wife and three young kids.